HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → {4-Methyl-2-[3-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}methanol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | ethyl 4-methyl-2-[3-(trifluoromethyl)phenyl]-1,3-thiazole-5-carboxylate | HCID 2774390 | — |
| Reactant | Sodium borohydride | HCID 4311764 | — |
| Reactant | Calcium Chloride | HCID 5284359 | — |
| Solvent | Tetrahydrofuran ethanol | HCID 21873804 | — |
| Product | {4-Methyl-2-[3-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}methanol | HCID 22647518 | 50% |
Reaction Steps
Under a nitrogen atmosphere at 0° C., to a mixed solution of the compound (380 mg, 1.2 mmol) obtained in Example 70a in ethanol/tetrahydrofuran (v/v=1/1, 6 mL) were added calcium chloride (500 mg, 4.5 mmol) and sodium tetrahydroborate (170 mg, 4.5 mmol), and the mixture was stirred at room temperature overnight. 1N Hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The resulting crude title compound was purified by column chromatography (hexane-hexane/ethyl acetate=65/35) to give the title compound (160 mg, 50%) as a colorless solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08461348B2 |
| Source dataset | uspto-grants-2013_06 |
| ORD ID | ord-1b38e857379d46ebbc263b32a70237a2 |
| Source note | uspto-grants-2013_06 |